(1R,2R,4S,5S,7R)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl (2S)-3-(acetyloxy)-2-phenylpropanoate hydrobromide

• ChemBase ID: 159460
• Molecular Formular: C19H24BrNO5
• Molecular Mass: 426.30156
• Monoisotopic Mass: 425.08378487
• SMILES: Br.O(C(=O)[C@@H](c1ccccc1)COC(=O)C)[C@H]1C[C@H]2[C@H]3[C@@H]([C@H](N2C)C1)O3
• Canonical SMILES: CC(=O)OC[C@H](c1ccccc1)C(=O)O[C@@H]1C[C@@H]2[C@@H]3[C@H]([C@H](C1)N2C)O3.Br
• InChI: InChI=1S/C19H23NO5.BrH/c1-11(21)23-10-14(12-6-4-3-5-7-12)19(22)24-13-8-15-17-18(25-17)16(9-13)20(15)2;/h3-7,13-18H,8-10H2,1-2H3;1H/t13-,14-,15-,16+,17-,18+;/m1./s1
• InChIKey: OBUFDYBDRQYWCZ-LBUMUNEBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,4S,5S,7R)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-7-yl (2S)-3-(acetyloxy)-2-phenylpropanoate hydrobromide
• IUPAC Traditional name: (1R,2R,4S,5S,7R)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-7-yl (2S)-3-(acetyloxy)-2-phenylpropanoate hydrobromide
• Synonyms: 6β,7β-Epoxy-1αH,5αH-tropan-3α-ol (-)-Tropate (Ester) Acetate Hydrobromide; Scopolamine Acetate Hydrobromide; (-)-Scopolamine Acetate Hydrobromide; NSC 172233; O-Acetyl-(-)-hyoscine Hydrobromide; O-Acetyl Scopolamine Hydrobromide

Database IDs

• CAS Number: 5027-67-8
• PubChem SID: 162253595
• PubChem CID: 71312993

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.12859574
• LogD (pH = 7.4): 1.2033216
• Log P: 1.3360777
• Molar Refractivity: 88.8728 cm^3
• Polarizability: 35.859093 Å^3
• Polar Surface Area: 68.37 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol (hot); Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - A187825

Scopolamine Hydrobromide (S200000) derivative. An acetylcholine antagonist. Used in treatment of motion sickness; antiemetic; antispasmodic; mydriatic; preanesthetic medicant.

REFERENCES

• Brand, J.J., et al.: Lancet, 2, 232 (1970)
• Bowles, J.B., et al.: Anaesthesia, 34, 476 (1970)
• Clissold, S.P., et al.: Drugs, 29, 189 (1970)
• Muhtadi, F.J., et al.: Anal. Profiles Drug Subs., 19, 477 (1970)